We have 84 self catering cottages for Christmas on the Isle of Wight
7 nights from £1000
Oak Tree Cottage
42123 bedroom self catering cottage with sea views in Seaview, Isle of Wight
With gorgeous views over the Solent and the beach just a few steps away, Oak Tree Cottage is a delightful reverse level holiday home situated a short stroll from the village centre...
7 nights from £1000
7 nights from £590
Grace Cottage
42091 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight
This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...
7 nights from £590
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £1758
Bayside House
41784 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight
This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes' walk to the water’s edge, a truly stunning holiday destination. The pro...
7 nights from £1758
7 nights from £897
Keepers Cottage
40704 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...
7 nights from £897
7 nights from £1194
The New House
40254 bedroom self catering cottage in Godshill, Isle of Wight
Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...
7 nights from £1194
7 nights from £944
St Albans House
39804 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...
7 nights from £944
7 nights from £908
Bay View
39022 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...
7 nights from £908
7 nights from £534
6 St Josephs
38462 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...
7 nights from £534
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
7 nights from £1174
Shore House
37783 bedroom self catering cottage with sea views in Seaview, Isle of Wight
Perfectly located in the charming village of Seaview on the Isle of Wight, with wonderful Solent views and the luxury of a private heated swimming pool, Shore House is a delightful...
7 nights from £1174
7 nights from £541
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...
7 nights from £541
